In The Trenches

Hosted by Steve Divitkos

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152

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Oct 2026

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About the show

The only podcast dedicated exclusively to Entrepreneurs and CEOs running Small to Medium Sized Businesses (SMB). Nobody knows what it’s like to be an Entrepreneur or CEO unless you’ve been one. Though many understand the rewards of company leadership, very few understand the arduous journey that’s required to get (and stay) there. I share my own lessons as an Entrepreneur and CEO, and interview experts spanning Sales, Leadership, Mental Health, M&A, and Operations (among others) all with a single goal: To improve the personal and professional lives of Entrepreneurs and CEOs running SMBs.

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October 28, 2026Episode 101 hr 17 min

The Unseen Realities of Selling Your Company to Private Equity

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Kilpatrick, a leading global law firm with a dedicated search fund team that works with searchers from inception, to acquisition, to exit⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ . * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click Here to Subscribe to the In The Trenches YouTube Channel⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * Today we dive deeply into the realities of selling your company to a private equity firm, and explore some of the less understood and underappreciated nuances of doing so. I was joined this week by Derek Bullard, who has founded and sold three separate private companies, all in the healthcare ecosystem. Two of those exits were to private equity firms, and one was to a strategic acquiror. Among other things, in our discussion today, we cover: How to differentiate between possible PE buyers in a competitive sales process Potential points of disagreement with a private equity parent after closing How PE firms think about target companies that have grown largely organically The characteristics that make a business particularly attractive to private equity, beyond obvious considerations like growth, profitability, and market size What is similar, and what is fundamentally different, between selling to PE versus selling to a strategic acquiror The personal considerations that the selling CEO needs to weigh when deciding which type of buyer to engage with How to manage confidentiality concerns when selling to a strategic acquiror, especially if they’re a competitor How to reconcile the risk of a strategic acquiror terminating some of the people who built the business to the point where it became an attractive acquisition candidate in the first place …and much, much more

October 15, 2026Episode 932 min

The Most Valuable A.I. Use Cases as Reported by Searchers, CEOs and Investors

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Kilpatrick, a leading global law firm with a dedicated search fund team that works with searchers from inception, to acquisition, to exit⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ . * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click Here to Subscribe to the In The Trenches YouTube Channel⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * Several weeks ago, I commissioned a survey that I sent to thousands of Searchers, CEOs, and investors across the SMB ecosystem. This was an anonymous, one-question survey that asked each respondent for their single highest-impact use case for A.I. thus far. The goal was for these use cases to be as tactical and as practical as possible, such that interested listeners could begin experimenting with similar use cases on that very same day. In today’s episode I present the results of that survey, organized into three categories of use cases: Searching, Operating, and Investing.

October 5, 2026Episode 81 hr 20 min

How to Apply Business Tools and Frameworks to Improve Your Personal Life

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Kilpatrick, a leading global law firm with a dedicated search fund team that works with searchers from inception, to acquisition, to exit⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ . * ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click Here to Subscribe to the In The Trenches YouTube Channel⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * For those of you who have experience running a small business, you’re likely aware of how powerful it can be to implement certain well-understood tools and frameworks to govern how you make decisions (things like Mission, Vision & Values, a regular meeting cadence, regularly scheduled one-on-ones, and so on). But to what extent have you considered implementing these tools in your personal life? My guest today, Blake Allsmith, is somebody who has gone to incredible lengths to implement what appear to be commercial tools and frameworks to drastically improve his family life. In our discussion today, we cover some of these tools, including: How Blake and his wife established his family’s mission and vision Examples of how the mere existence of a mission & vision have impacted their daily lives How and why his family codified their core values, and how he ensures that they are meaningful and impactful His family’s meeting cadence, covering daily, weekly, quarterly, and annual meetings, and how the nature of the discussions change depending on the type of meeting being held How his family practices radical candor internally, and a united front externally How he uses a 2x2 matrix to govern how and when to settle disagreements between family members His suggestion for the single tool that all families should adopt from his practice, even if they were to ignore the rest of them And much, much more

September 17, 2026Episode 741 min

Who to Hire and Who to Fire

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Kilpatrick, a leading global law firm with a dedicated search fund team that works with searchers from inception, to acquisition, to exit⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ . * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click Here to Subscribe to the In The Trenches YouTube Channel⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This week, I’ve combined two blog posts into a single episode, as the two topics that we’ll explore are so central to the job of any small business CEO: In Part 1, I walk you through the most meaningful lessons that I learned as a CEO related to hiring. In Part 2, we explore the opposite side of the coin, and discuss how, when, and who to fire. Hiring and retaining the right people (as well as moving out the wrong people) is arguably the most important job of any CEO, and I’d argue that it’s particularly important within the context of a small business, where a single individual can represent as much at 5-10% of the total employee base. If, in a hypothetical world, you could only focus on one thing as a leader, I might argue that this is it. I hope that you’ll find at least some of my reflections, mistakes and lessons to be applicable to your own situation.

September 3, 2026Episode 61 hr 20 min

The Case for Focus, Profitability, and Saying No to Growth for Its Own Sake

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Kilpatrick, a leading global law firm with a dedicated search fund team that works with searchers from inception, to acquisition, to exit⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ . * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click Here to Subscribe to the In The Trenches YouTube Channel⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * Today’s guest is Chris Hillier, an entrepreneur, investor, author, and longtime operator in the world of small and mid-sized businesses. He was the co-founder of a company called Benefit Health Advisor, which he started with his brother and father in the midst of the Great Recession. Over the subsequent sixteen years, he grew revenue at a staggering rate of 30% annually, and grew EBITDA by more than 40% annually over that same period. Along the way, Chris acquired a struggling insurance underwriting business that was nearing shutdown, helped grow it nearly fifteenfold, and ultimately sold both businesses in 2018, after which he spent five years inside of the larger organization that had acquired him. Today, Chris invests in and advises entrepreneurs, teaches at the University of Denver, and is the author of "It’s About Time" and "Built Different". Our conversation today covers growth, the benefits of specialization, the revenue growth vs profitability trade-off, time management at both a personal and professional level, and how his views on ambition, family, and success have evolved after his exit.

August 20, 2026Episode 51 hr 31 min

A Cybersecurity Survival Guide for Small Businesses

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Kilpatrick, a leading global law firm with a dedicated search fund team that works with searchers from inception, to acquisition, to exit⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ . * ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click Here to Subscribe to the In The Trenches YouTube Channel⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * * Download your free copy of Kip's Book, Fire Doesn’t Innovate * In 2026, you probably don’t need to look terribly far to read about both the frequency and seriousness of cyber attacks on both individuals and small businesses. Because of how unfortunately common these attacks have become, and because of how difficult they can be to understand if not explained at an appropriate level of detail, I thought it would be worthwhile to dedicate an entire episode to discussing “Cybersecurity 101" for Small Businesses. To help me, I was joined by Kip Boyle, a security expert with 25 years of experience in cybersecurity and IT risk management for organizations in insurance, financial services, technology, military, and logistics, among others. Prior to his current role as a consultant and fractional chief information security officer for small businesses, Kip spent many years as the Chief Information Security Officer at PEMCO Insurance and has also served as the Chief Security Officer of a transaction processing business, and an IT services provider to financial institutions.

August 6, 2026Episode 41 hr 18 min

A Glimpse Into The First 90 Days as a New CEO

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠Kilpatrick, a leading global law firm with a dedicated search fund team that works with searchers from inception, to acquisition, to exit⁠⁠⁠⁠⁠⁠⁠⁠ . * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * ⁠⁠⁠⁠⁠⁠⁠⁠⁠Click Here to Subscribe to the In The Trenches YouTube Channel⁠⁠⁠⁠⁠⁠⁠⁠⁠ * You probably don’t need to have much of an imagination to envision just how intimidating it can be to be a first-time CEO within your first 90 days. I remember my own such experience like it was yesterday, and still remember it as a time in my life where I was, paradoxically, both excited and insecure, confident and fearful, relieved and anxious, tired and energized. How to approach the first 90 days as a new CEO, including what to do and what not to do, is also among the most frequently asked questions that I’ve received over the past 14 years. For this reason, I thought it would be a great idea to interview 3 CEOs, each at different stages of their leadership journeys, and ask each of them the same 3 questions: Their general approach to the first 30 days What worked What didn’t work I think you’ll find their answers to be highly instructive, particularly the themes that seemed to be consistent across all 3 of their stories. Today I was joined by John O’Brien, CEO of Echo Point Books & Media, Matt Fiedelholtz, co-CEO of Stage 2 Data, and Ethan Walz, co-CEO of Allied Electric. Please enjoy!

July 23, 2026Episode 353 min

The Most Meaningful Lesson that I've Learned Over the Past 12 Months

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠Kilpatrick, a leading global law firm with a dedicated search fund team that works with searchers from inception, to acquisition, to exit⁠⁠⁠⁠⁠⁠⁠ . * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * ⁠⁠⁠⁠⁠⁠⁠⁠Click Here to Subscribe to the In The Trenches YouTube Channel⁠⁠⁠⁠⁠⁠⁠⁠ * Regular listeners of the show will know that I often conclude with the same question: “ What is the most meaningful lesson that you have learned over the past 12 months, across any domain of your life? ”. I’ve received so many interesting answers to this question that I decided to compile them into a single episode, that features the answers of 15 of our previous guests. One of my favorite quotes is “we need to be reminded more than we need to be taught”, which suggests that many of our most meaningful lessons are ones that we already know at some level, but often need to experience to fully appreciate their importance. What I loved most about today’s episode is not just how simple and fundamental the answers were, but also how they spanned so many different domains of life: Business, personal, family, and spiritual, just to name a few.

July 9, 2026Episode 21 hr 24 min

A Peek Behind the Curtain: What Small Business Ownership Really Looks Like

This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠Kilpatrick, a leading global law firm with a dedicated search fund team that works with searchers from inception, to acquisition, to exit⁠⁠⁠⁠⁠⁠ . ⁠⁠⁠⁠⁠⁠⁠Click Here to Subscribe to the In The Trenches YouTube Channel⁠⁠⁠⁠⁠⁠⁠ * Since the first blog post that I wrote in April of 2021, I have been rather public with my opinion that nobody knows what it’s like to be an entrepreneur or CEO unless you’ve been one. Personally, and professionally, we face both challenges and opportunities that few others can relate to. Though many understand the rewards of company leadership (things like compensation, decision making authority, and independence) few understand the sometimes-arduous journey that’s required to both get there, and to stay there. This is why it can feel genuinely lonely at the top: In spite of their best efforts, our spouses, direct reports, and friends simply don’t understand what it’s really like. More accurately, they can’t be expected to. The point of today’s episode is to give the uninitiated a peak behind the curtains, and to provide but one example of what leadership really looks like at the ground level. My guest today, Rishi Sahel, is a great example of a CEO who has withstood more than his share of punches to the gut: As you’ll hear in our discussion today, these punches included (but were not limited to) an acquisition of a manufacturing company in the middle of Covid when lockdown orders were in full effect, a post-covid supply chain crisis, Post-covid runaway inflation, a Lost warehouse, an attempt to buy their primary manufacturing facility from out underneath them, wire fraud, tariffs impacting a global supply chain and global customer base, and one unforgettable presentation to members of a local city council – all of which is about a million miles away from the comfortable confines of Bain, where Rishi spent many years prior to pursuing his dream of acquiring a small business. As you’ll hear, despite all of these challenges, the company that he has built has enjoyed incredible growth and success. But hopefully better understanding the details of his journey will give you pause the next time you’re tempted to get too enamoured with what seems to be an unambiguously positive headline. In presenting Rishi’s story to you, I don’t at all mean to suggest that leadership is all downside and no upside. Quite the contrary, in fact. Instead, I’m providing you with this dose of reality only because I assume you’re much more familiar with the upsides of entrepreneurship and leadership, and much less familiar with the price that you’re likely to have to pay in order to receive those benefits.

June 25, 2026Episode 11 hr 11 min

$2B Company Founder on Youth, Inexperience, and Why You're More Ready Than You Think

This episode is brought to you by ⁠⁠⁠⁠Kilpatrick, a leading global law firm with a dedicated search fund team that works with searchers from inception, to acquisition, to exit⁠⁠⁠⁠ . * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * This episode is brought to you by ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Oberle Risk Strategies⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ * ⁠⁠⁠⁠⁠⁠Click Here to Subscribe to the In The Trenches YouTube Channel⁠⁠⁠⁠⁠⁠ * My guest today is Ronnen Harary, the Co-Founder and Chairman of Spin Master Toys, the fourth-largest toy company in the world behind only Lego, Mattel, and Hasbro. Alongside his business partners, Ronnen co-founded Spin Master in 1994 and eventually transformed it from a three-person startup into a publicly traded company with a market capitalization of ~$2B, generating ~$2.3B in annual revenue. In our conversation today, we talk about the four major themes that stuck out to me from Ronnen’s career: 1. Youth, inexperience and how that frames how we ought to think about taking risk in our lives and careers 2. Tail events: The impact of a small number of outcomes that generate a disproportionate share of results 3. Relationships between business partners: How he thinks about what makes for a great partnership (and what makes for a bad one) 4. Once you've accomplished your wildest dreams, what happens to your relationship with risk and ambition?